80945-33-1

Upstream product

• 3112-85-4 methylphenylsulfonate 
• 818-57-5 Methyl 4-pentenoate 
• 599-70-2 ethyl phenyl sulfone 
• 80945-24-0 2-(trimethylsilylmethyl)-1-(1-oxo-2-phenylsulfonylethyl)cyclopropane 
• 55454-02-9 sodium salt of methyl phenyl sulfone 
• 80945-29-5 2-(trimethylsilylmethyl)-1-(1-oxo-2-phenylsulfonylpropyl)cyclopropane 
• 123209-23-4 1-<<1-methyl-2-(2-propenyloxy)-2-propenyl>sulfonyl>benzene 

Downstream Products

• 1134193-20-6 C₁₅H₁₈O₄S 

Relevant academic research and scientific papers

SULFONAMIDE-BASED ORGANOCATALYSTS AND METHOD FOR THEIR USE

Organocatalysts, particularly proline sulfonamide organocatalysts, having a first general formula as follows are disclosed. Embodiments of a method for using these organocatalysts also are disclosed. The method comprises providing a disclosed organocataly

Development of an enantioselective route toward the lycopodium alkaloids: Total synthesis of lycopodine

(Figure presented) Synthesis of a C15-desmethyl tricycle core of lycopodine has been accomplished. Key steps in the synthetic sequence include organocatalytic, intramolecular Michael addition of a keto sulfone and a tandem 1,3-sulfonyl shift/Mannich cyclization to construct the tricyclic core ring system. Synthetic work toward this natural product family led to the development of N-(p-dodecylphenylsulfonyl)-2-pyrrolidinecarboxamide, an organocatalyst which facilitiates enantioselective, intramolecular Michael additions. A detailed mechanistic discussion is provided for both the intramolecular Michael addition and the sulfone rearrangement. Finally, the application of these discoveries to the enantioselective total synthesis of alkaloid lycopodine is described.

Carbanion-Accelerated Claisen Rearrangements. 6. Preparative and Stereochemical Studies with Sulfonyl-Stabilized Anions

The aliphatic Claisen rearrangement is markedly accelerated by an arylsulfonylmethide substituent at position 2.The generality of this anion variant has been extensively examined (31 allyl vinyl ethers) with regard to substitution, stereochemistry, and an

Silicon-Assisted Ring Opening of Cyclopropyl Ketones with Boron Trifluoride-Acetic Acid Complex

2-(Trimethylsilylmethyl)cyclopropyl ketones were smoothly cleaved with boron trifluoride-acetic acid complex under mild reaction conditions with the assistance of the trimethylsilyl group to give γ,δ-enones in good yields.The major effect of the trimethylsilyl group in the ring opening of the cyclopropyl ketones was unambiguously confirmed in the dicyclopropyl ketone 15: one of its two cyclopropyl rings, which has a trimethylsilylmethyl group, was selectively cleaved.Furthermore, the reaction was applied to the formal total synthesis of cis-jasmone.Keywords - ring opening of cyclopropyl ketone; trimethylsilyl group; γ,δ-enone; cis-jasmone; allylsilane; boron trifluoride-acetic acid

RING OPENING OF CYCLOPROPYL KETONES ASSISTED BY THE TRIMETHYLSILYL GROUP

Cyclopropyl ketones 2 were smoothly cleaved with boron trifluoride-acetic acid under mild reaction conditions by the assistance of trimethylsilyl group to give γ,δ-enones in good yields and the reaction was applied to the formal total synthesis of cis-jasmone.